EP0409280A2 - Composition d'élastomère de silicone pour le traitement de structures fibreuses - Google Patents

Composition d'élastomère de silicone pour le traitement de structures fibreuses Download PDF

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Publication number
EP0409280A2
EP0409280A2 EP90113983A EP90113983A EP0409280A2 EP 0409280 A2 EP0409280 A2 EP 0409280A2 EP 90113983 A EP90113983 A EP 90113983A EP 90113983 A EP90113983 A EP 90113983A EP 0409280 A2 EP0409280 A2 EP 0409280A2
Authority
EP
European Patent Office
Prior art keywords
parts
weight
component
hours
silicone rubber
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP90113983A
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German (de)
English (en)
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EP0409280A3 (en
EP0409280B1 (fr
Inventor
Isao Ona
Masaru Ozaki
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DuPont Toray Specialty Materials KK
Original Assignee
Dow Corning Toray Silicone Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Corning Toray Silicone Co Ltd filed Critical Dow Corning Toray Silicone Co Ltd
Publication of EP0409280A2 publication Critical patent/EP0409280A2/fr
Publication of EP0409280A3 publication Critical patent/EP0409280A3/en
Application granted granted Critical
Publication of EP0409280B1 publication Critical patent/EP0409280B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
    • C08K13/02—Organic and inorganic ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups

Definitions

  • the present invention concerns silicone rubber compositions for treatment of fiber structures, such as woven fabric, knit fabric, nonwoven fabric, etc. More specifically, the present invention relates to silicone rubber compositions for treatment of fiber structures, having long pot life and imparting films of excellent tensile strength, tear strength, and abrasion resistance.
  • Fiber structures such as woven fabrics, knit fabrics and nonwoven fabrics, treated (especially coated) with conventional silicone rubbers are soft with excellent water- repellency, water-pressure resistance and also high moisture permeability. Thus they have been widely used in diaper covers, snow wear, mountain wear, sports wear, raincoats, tents, etc.
  • the silicone rubbers used for coating fiber structures are, e.g., addition reaction-curable silicone rubbers (Japanese Kokai Patents Nos. Sho 58(1983)-171937, Sho 60(1985)-51754 and Sho 57(1982)-165069) and condensation reaction-curable silicone rubber (Japanese Kokai Patent No. Sho 53(1978)-94693).
  • silicone rubbers have some strong points and also some weak points, and both long pot life and desirable physical properties cannot be obtained at the same time.
  • addition reaction-curable silicone rubbers form films with good tensile strength, tear strength, abrasion resistance, etc., while their adhesion to fiber structure is weak, and curing may be adversely affected by small amounts of surfactants and other impurities of phosphorus, nitrogen, sulfur compounds adhered to the fiber during processing of fibers or fabrics.
  • condensation reaction-curable silicone rubbers show good adhesion to the fiber structure, while tensile strength, tear strength and abrasion resistance are not sufficient.
  • a silicone rubber composition for treatment of fiber structures comprising:
  • the organopolysiloxane used for the component A is the main component of the coating materials of the present invention and is essentially a linear polysiloxane represented by the general formula HO(R2SiO) n H wherein R is a substituted or unsubstituted monovalent hydrocarbon group and the subscript n is a number in the 50-10,000 range.
  • R represents an alkyl group such as methyl, ethyl, propyl, butyl, octyl, etc.; an alkenyl group such as vinyl, allyl, etc.; an aryl group such as phenyl, tolyl, etc.; a substituted alkyl group such as 3,3,3-trifluoropropyl, 3- chloropropyl, etc.
  • Organopolysiloxane A may be a homopolymer, a copolymer, or mixtures of two or more polymers.
  • the alkenyl group-terminated organopolysiloxane of component B is not an essential component; however, it enhances the elongation of the film when cured together with the component A.
  • a vinyl group is especially preferred for alkenyl group.
  • Other organic groups include those given for R above.
  • the degree of polymerization is preferably above 50, more preferably above 1,000, namely, organopolysiloxane rubber. Based on 100 parts by weight of component A, the amount of component B added is 0-50 parts by weight, preferably 5-30 parts by weight.
  • the inorganic fillers used as component C are needed for enhancing tensile strength, tear strength and abrasion resistance of cured film. While fumed silica is preferred, dry-process silica, wet-process silica, finely powdered quartz, titanium dioxide, calcium carbonate, kieselguhr, carbon black, etc., can be also be used. They may be use as mixtures of two or more, and they may be surface-treated with silanes, silazanes, low-molecular-weight polysiloxanes, organic compounds, etc. Based on 100 parts by weight of component A, the amount of component C added is 3-100 parts by weight, preferably 5-50 parts by weight.
  • the organopolysiloxane used as component D in the present invention is the crosslinking agent for component A and is linear, branched, or cyclic organohydrogenpolysiloxane of units of general formula R a H b SiO (4-a-b)/2 wherein R is substituted or unsubstituted monovalent hydrocarbon group as defined above; a is 1-3; b is 0.5-1, containing at least 3 hydrogen atoms bonded to different silicon atoms.
  • the amount of component D used is 0.1-20 parts by weight, preferably 0.5-10 parts by weight.
  • the mercaptoalkyl group-containing di- or trialkoxysilane used as component E in the present invention is needed for pot life extension and can be represented by the general formula HS(CH2) d Si(R) e (OR1) 3-e wherein R is a substituted or unsubstituted monovalent hydrocarbon group as given above; R1 is an alkyl group of 1-5 carbon atoms; d is 2-6; e is 0 or 1. Preferably, d is 3, and R or R1 is an alkyl group of 1-3 carbon atoms.
  • component E Based on 100 parts by weight of component A, the amount of component E used is 0.1-20 parts by weight, preferably 0.5-10 parts by weight.
  • the aliphatic monohydroxy alcohol used as component F is also a pot life-extending component used with component E; aliphatic monohydroxy alcohols of 1-5 carbon atoms are preferred. Especially, for component F, monohydroxy alcohols of 1-3 carbon atoms are preferred because they are readily evaporated upon heating without leaving any residues on fibers or any odor. Ethyl alcohol is most preferred. Based on 100 parts by weight of component A, the amount of component F used is 0.1-30 parts by weight, preferably 0.5-20 parts by weight.
  • the curing catalyst used for component G is a condensation reaction catalyst and promotes reaction between component A (also component B if present) and component D.
  • the condensation reaction catalysts are organometallic catalysts and amine catalysts.
  • Organometallic catalysts are metal salts of organic acids, e.g., dibutyltin diacetate, dibutyltin dilaurate, dioctyltin dilaurate, dibutyltin dioctoate, zinc naphthenate, tin octylate, cobalt octylate, diisooctyltin dioctylate, zirconium naphthenate, zirconium octylate, tetrabutyl orthotitanate, etc.
  • Amine catalysts are, e.g., di- and triethanolamine. Based on 100 parts by weight of component A, the amount of component F used is 0.2-20 parts by weight, preferably 0.5-10 parts
  • the solvents used as component H in the present invention are used in making the compositions of the present invention into dispersions for easy application on fiber structure, e.g., aromatic hydrocarbon solvents such as toluene, xylene, benzene, etc.; chlorine-containing solvents such as carbon tetrachloride, trichloroethylene, 1,1,1- trichloroethane, tetrachloroethylene, etc.; aliphatic hydrocarbon solvents such as hexane, heptane, etc. Among them, aromatic solvents and chlorine solvents are preferred. While the amount of component H used varies as needed for ease of coating application, it is usually 50-2,000 parts by weight, preferably 100-1,000 parts by weight based on 100 parts by weight of component A.
  • various additives may be added, such as various silane couplers for enhanced adhesion, hydroxy-terminated low-molecular-weight organopolysiloxanes as plasticizers, triorganosilyl group-terminated silicone oils for imparting lubricity and softness to the film, pigments, dyes, antimildew agents, etc.
  • the fiber structures are woven, knit, nonwoven fabrics, etc., of natural fibers such as cotton, jute, wool, silk, etc., regenerated fibers such as rayon, semisynthetics such as acetate, etc., synthetic fibers such as nylons, polyesters, acrylics, vinyl chloride, polyethylene, polypropylene, Spandex, etc., and their blends.
  • films are formed by gravure or knife coating on the fiber structure and cured by heat.
  • a silicone rubber composition of the present invention is coated on a Teflon sheet, etc., adhered to a fiber structure and heat- cured for adhesion of the silicone rubber to the fiber structure.
  • immersion or spray method may be used. After solvents are evaporated, the treated fiber structures are heated at 100-200°C for 1-5 min to form a silicone rubber film on the fiber structure, with good toughness and moisture permeability.
  • the fiber structure treated with the silicone rubber compositions of the present invention have good toughness and moisture permeability, thus are useful for diaper covers, snow wear, mountain wear, sports wear, raincoat, tent, etc.
  • the dispersion (I) used in Application Example 1 was treated with 1.5 parts of ethyl alcohol and various amounts of HS(CH2)3Si(CH3)(OCH3)2. Then changes in viscosity with time was measured as in Application Example 1 with observation of states of coating and film. For comparison, the process was repeated using 1.5 parts of ethyl alcohol, but without HS(CH2)3Si(CH3)(OCH3)2. The results are given in Table II. The composition with only ethyl alcohol was found to be gelled after 30 min, while the compositions treated with both ethyl alcohol and HS(CH2)3Si(CH3)(OCH3)2 showed stable viscosity even after 10 hours with good coatability and state of film.
  • Rubber base (II) was prepared under the conditions of Application Example 1, except that 90 parts of the hydroxy- terminated dimethylpolysiloxane with molecular weight 520,000 used in Application Example 1 and 10 parts of vinyl group- terminated dimethylpolysiloxane of molecular weight 55000 were used.
  • Dispersion (II) was prepared under the same conditions of Application Example 1 from 100 parts of the rubber base (II).
  • dispersion (II) 100 parts was treated with 1 part of dibutyltin diacetate catalyst and 25 parts of toluene as viscosity control agent. As shown in Table III, the mixture was stirred with 2 parts of HS(CH2)3Si(CH3)(OCH3)2, 0.5, 2.5, or 5.0 parts of ethyl alcohol. Similar to Application Example 1, the change in viscosity with time was measured and coating films were prepared.
  • Rubber bases (III), (IV), (V), and (VI) were prepared from 90 parts of dimethyl polysiloxane having hydroxyl groups at the ends of molecular chains with molecular weight of about 520,000 used in Application Example 3, 10 parts of dimethyl polysiloxane having vinyl groups at the ends of molecular chains with molecular weight of about 55,000 used in Application Example 3, as well as 5.25 parts (5% with respect to the weight of polysiloxane), 11.11 parts (10% with respect to the weight of polysiloxane), 17.64 parts (15% with respect to the weight of polysiloxane), and 25.0 parts (20% with respect to the weight of polysiloxane) of fumed silica and a specific surface area of 300 m2/g (Aerosil 300, Nippon Aerosil Co., Ltd), respectively.
  • rubber base (VII) was prepared without adding the fumed silica.
  • 100 parts were taken to prepare dispersions (III)-(VII) according to Application Example 1.
  • 25 parts of toluene were added to 100 parts of the dispersion. In this case, however, it was not added, while 1.0 part of dibutyltin di(2-ethylhexoate) as well as 2.0 part of HS(CH2)3Si(CH3)(OCH3)2 listed in Table IV and 3.0 parts of ethyl alcohol were added.
  • the variation in time of the viscosity was measured in the same way as in Application Example 1.
  • condensation reaction-curing silicone rubber compositions of the present invention containing mercaptoalkyl group-containing di- or trialkoxysilanes and aliphatic monohydroxy alcohols are free from drawbacks of addition reaction curing type and, even when inorganic filler content is increased in dispersion, viscosity stability was excellent, and high-strength films are readily obtained.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Textile Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Reinforced Plastic Materials (AREA)
EP90113983A 1989-07-21 1990-07-20 Composition d'élastomère de silicone pour le traitement de structures fibreuses Expired - Lifetime EP0409280B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP1190090A JPH0359174A (ja) 1989-07-21 1989-07-21 繊維構造物処理用シリコーンゴム組成物
JP190090/89 1989-07-21

Publications (3)

Publication Number Publication Date
EP0409280A2 true EP0409280A2 (fr) 1991-01-23
EP0409280A3 EP0409280A3 (en) 1992-03-04
EP0409280B1 EP0409280B1 (fr) 1994-11-09

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ID=16252202

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90113983A Expired - Lifetime EP0409280B1 (fr) 1989-07-21 1990-07-20 Composition d'élastomère de silicone pour le traitement de structures fibreuses

Country Status (6)

Country Link
US (1) US5126389A (fr)
EP (1) EP0409280B1 (fr)
JP (1) JPH0359174A (fr)
AU (1) AU633335B2 (fr)
CA (1) CA2021153C (fr)
DE (1) DE69013999T2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992009659A1 (fr) * 1990-11-21 1992-06-11 Presstek, Inc. Formulations de revetement de silicone et plaques d'impression planographiques produites avec ledit revetement
EP0643106A2 (fr) * 1993-09-10 1995-03-15 Shin-Etsu Chemical Co., Ltd. Compositions d'organopolysiloxanes, leur préparation et emploi et des objets en caoutchouc ayant un revêtement organopolysiloxane
EP1449858A3 (fr) * 2003-02-13 2004-10-13 Hermann Otto GmbH Composition de silicone réticulable par condensation
CN108314989A (zh) * 2018-02-26 2018-07-24 重庆建工第七建筑工程有限责任公司 一种净化空调风管密封胶及其制备方法

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0811870B2 (ja) * 1991-05-14 1996-02-07 信越化学工業株式会社 パラグライダー用基布処理剤組成物及びそれを用いたパラグライダー用キャノピー素材
AU2824795A (en) * 1994-06-30 1996-01-25 Procter & Gamble Company, The Fluid transport webs exhibiting surface energy gradients
DE19545365A1 (de) * 1995-12-05 1997-06-12 Wacker Chemie Gmbh Verfahren zur Herstellung lagerstabiler oxidische verstärkende Füllstoffe enthaltender Organopolysiloxanzusammensetzungen
DE19735813A1 (de) * 1997-08-18 1999-02-25 Wacker Chemie Gmbh Kompressiblen Schwefel enthaltender Siliconkautschuk
FR2946365A1 (fr) * 2009-06-05 2010-12-10 Bluestar Silicones France Procede d'enduction d'un support textile
JP2012041428A (ja) * 2010-08-18 2012-03-01 Shin-Etsu Chemical Co Ltd シリコーン樹脂組成物及び光半導体ケース
US10563015B2 (en) 2015-01-28 2020-02-18 Dow Silicones Corporation Elastomeric compositions and their applications
WO2017183259A1 (fr) * 2016-04-22 2017-10-26 株式会社Adeka Composition durcissable comportant du silicium et objet durci obtenu à partir de la composition durcissable
GB201613397D0 (en) 2016-08-03 2016-09-14 Dow Corning Cosmetic composition comprising silicone materials
GB201613414D0 (en) 2016-08-03 2016-09-14 Dow Corning Elastomeric compositions and their applications
GB201613412D0 (en) 2016-08-03 2016-09-14 Dow Corning Elastomeric compositions and their applications
GB201613399D0 (en) 2016-08-03 2016-09-14 Dow Corning Cosmetic composition comprising silicone materials
GB201707437D0 (en) 2017-05-09 2017-06-21 Dow Corning Lamination adhesive compositions and their applications
GB201707439D0 (en) 2017-05-09 2017-06-21 Dow Corning Lamination Process
US11760847B2 (en) * 2022-01-25 2023-09-19 Green Theme Technologies, Inc. Solid-state method for treating polyamide and polyester articles

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0073446A1 (fr) * 1981-08-25 1983-03-09 Wacker-Chemie GmbH Caoutchouc à base de silicone ayant une formation de peau retardée
EP0112396A1 (fr) * 1982-06-15 1984-07-04 Toray Silicone Co., Ltd. Composition permettant de former une pellicule detachable
EP0261418A2 (fr) * 1986-08-25 1988-03-30 Toray Silicone Company, Ltd. Matériel d'étanchéité ayant une adhérence excellente et résistant aux agents de refroidissement

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US3957714A (en) * 1975-05-19 1976-05-18 Dow Corning Corporation Method for making paintable silicone surfaces and elastomer
JPS5331761A (en) * 1976-09-07 1978-03-25 Toray Silicone Co Ltd Thermosetting silicone resin composition
DE3108595A1 (de) * 1981-03-06 1982-09-16 Wacker-Chemie GmbH, 8000 München Verfahren zur beschichtung von unterlagen
US4430466A (en) * 1982-02-22 1984-02-07 Phillips Petroleum Company Benzothiazyl sulfenamides as scorch retardants for mercaptosilane-coupled silica filled-rubber compounds
US4474908A (en) * 1982-05-27 1984-10-02 Ppg Industries, Inc. Rubber compositions
US4500584A (en) * 1983-07-07 1985-02-19 General Electric Company Transparent membrane structures
JPS62223264A (ja) * 1986-03-25 1987-10-01 Shin Etsu Chem Co Ltd 室温硬化性オルガノポリシロキサン組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0073446A1 (fr) * 1981-08-25 1983-03-09 Wacker-Chemie GmbH Caoutchouc à base de silicone ayant une formation de peau retardée
EP0112396A1 (fr) * 1982-06-15 1984-07-04 Toray Silicone Co., Ltd. Composition permettant de former une pellicule detachable
EP0261418A2 (fr) * 1986-08-25 1988-03-30 Toray Silicone Company, Ltd. Matériel d'étanchéité ayant une adhérence excellente et résistant aux agents de refroidissement

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992009659A1 (fr) * 1990-11-21 1992-06-11 Presstek, Inc. Formulations de revetement de silicone et plaques d'impression planographiques produites avec ledit revetement
US5212048A (en) * 1990-11-21 1993-05-18 Presstek, Inc. Silicone coating formulations and planographic printing plates made therewith
EP0643106A2 (fr) * 1993-09-10 1995-03-15 Shin-Etsu Chemical Co., Ltd. Compositions d'organopolysiloxanes, leur préparation et emploi et des objets en caoutchouc ayant un revêtement organopolysiloxane
EP0643106A3 (fr) * 1993-09-10 1996-01-24 Shinetsu Chemical Co Compositions d'organopolysiloxanes, leur préparation et emploi et des objets en caoutchouc ayant un revêtement organopolysiloxane.
EP1449858A3 (fr) * 2003-02-13 2004-10-13 Hermann Otto GmbH Composition de silicone réticulable par condensation
CN108314989A (zh) * 2018-02-26 2018-07-24 重庆建工第七建筑工程有限责任公司 一种净化空调风管密封胶及其制备方法

Also Published As

Publication number Publication date
US5126389A (en) 1992-06-30
AU633335B2 (en) 1993-01-28
JPH0359174A (ja) 1991-03-14
EP0409280A3 (en) 1992-03-04
AU5986590A (en) 1991-01-24
DE69013999T2 (de) 1995-04-20
CA2021153C (fr) 1991-01-22
CA2021153A1 (fr) 1991-01-22
EP0409280B1 (fr) 1994-11-09
DE69013999D1 (de) 1994-12-15

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